AM-1241

AM-1241

Legal status
Legal status	CA: Schedule II
Identifiers
IUPAC name (2-iodo-5-nitrophenyl)-[1-[(1-methylpiperidin-2-yl)methyl]indol-3-yl]methanone
CAS Number	444912-48-5 N
PubChem CID	10141893
IUPHAR/BPS	3316
ChemSpider	8317404 Y
ChEMBL	CHEMBL408430 Y
ECHA InfoCard	100.164.689
Chemical and physical data
Formula	C22H22IN3O3
Molar mass	503.333 g/mol
3D model (Jmol)	Interactive image
SMILES Ic2ccc(N(=O)=O)cc2C(=O)c(c4ccccc14)cn1CC3CCCCN3C
InChI InChI=1S/C22H22IN3O3/c1-24-11-5-4-6-16(24)13-25-14-19(17-7-2-3-8-21(17)25)22(27)18-12-15(26(28)29)9-10-20(18)23/h2-3,7-10,12,14,16H,4-6,11,13H2,1H3 Y Key:ZUHIXXCLLBMBDW-UHFFFAOYSA-N Y
NY (what is this?)

AM-1241 (1-(methylpiperidin-2-ylmethyl)-3-(2-iodo-5-nitrobenzoyl)indole) is a chemical from the aminoalkylindole family that acts as a potent and selective agonist for the cannabinoid receptor CB₂, with a K_i of 3.4nM at CB₂ and 80x selectivity over the related CB₁ receptor. It has analgesic effects in animal studies, particularly against "atypical" pain such as hyperalgesia and allodynia. This is thought to be mediated through CB₂-mediated peripheral release of endogeous opioid peptides, as well as direct activation of the TRPA1 channel. It has also shown efficacy in the treatment of amyotrophic lateral sclerosis in animal models.

The antihyperalgesic effects of AM-1241 were investigated in a murine bone cancer model. Sarcoma cells were injected into the femur of a mouse, and then mice were injected twice daily with AM-1241. Treatment with AM-1241 reduced both spontaneous and evoked pain, as well as reducing the bone loss and subsequent fractures due to the tumor. Pretreatment with the CB₂ antagonist SR-144,528 reversed the acute effects of AM-1241 on both spontaneous and evoked pain, while having no effect on its own.